Identification
- Summary
Desipramine is a tricyclic antidepressant used in the treatment of depression.
- Brand Names
- Norpramin
- Generic Name
- Desipramine
- DrugBank Accession Number
- DB01151
- Background
Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Desipramine (DB01151)
- Weight
- Average: 266.3807
Monoisotopic: 266.178298714 - Chemical Formula
- C18H22N2
- Synonyms
- 5-(gamma-methylaminopropyl)iminodibenzyl
- 5-(γ-methylaminopropyl)iminodibenzyl
- Déméthylimipramine
- Desipramin
- Desipramina
- Desipramine
- Désipramine
- Desipraminum
- Desmethylimipramine
- DMI
- Monodemethylimipramine
- N-(3-methylaminopropyl)iminobibenzyl
- Norimipramine
Pharmacology
- Indication
For relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Anorexia nervosa ••• ••••• Treatment of Bulimia nervosa ••• ••••• Management of Chronic pain ••• ••••• Treatment of Depression •••••••••••• Treatment of Diabetic neuropathy ••• ••••• - Contraindications & Blackbox Warnings
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Desipramine, a secondary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is the active metabolite of imipramine, a tertiary amine TCA. The acute effects of desipramine include inhibition of noradrenaline re-uptake at noradrenergic nerve endings and inhibition of serotonin (5-hydroxy tryptamine, 5HT) re-uptake at the serotoninergic nerve endings in the central nervous system. Desipramine exhibits greater noradrenergic re-uptake inhibition compared to the tertiary amine TCA imipramine. In addition to inhibiting neurotransmitter re-uptake, desipramine down-regulates beta-adrenergic receptors in the cerebral cortex and sensitizes serotonergic receptors with chronic use. The overall effect is increased serotonergic transmission. Antidepressant effects are typically observed 2 - 4 weeks following the onset of therapy though some patients may require up to 8 weeks of therapy prior to symptom improvement. Patients experiencing more severe depressive episodes may respond quicker than those with mild depressive symptoms.
- Mechanism of action
Desipramine is a tricyclic antidepressant (TCA) that selectively blocks reuptake of norepinephrine (noradrenaline) from the neuronal synapse. It also inhibits serotonin reuptake, but to a lesser extent compared to tertiary amine TCAs such as imipramine. Inhibition of neurotransmitter reuptake increases stimulation of the post-synaptic neuron. Chronic use of desipramine also leads to down-regulation of beta-adrenergic receptors in the cerebral cortex and sensitization of serotonergic receptors. An overall increase in serotonergic transmission likely confers desipramine its antidepressant effects. Desipramine also possesses minor anticholinergic activity, through its affinity for muscarinic receptors. TCAs are believed to act by restoring normal levels of neurotransmitters via synaptic reuptake inhibition and by increasing serotonergic neurotransmission via serotonergic receptor sensitization in the central nervous system.
Target Actions Organism ASodium-dependent noradrenaline transporter inhibitorHumans ASodium-dependent serotonin transporter inhibitorHumans A5-hydroxytryptamine receptor 2A antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UBeta-1 adrenergic receptor otherHumans USphingomyelin phosphodiesterase inhibitorHumans NHistamine H1 receptor antagonistHumans NAlpha-1 adrenergic receptors antagonistHumans NMuscarinic acetylcholine receptor M1 antagonistHumans NMuscarinic acetylcholine receptor M2 antagonistHumans NMuscarinic acetylcholine receptor M3 antagonistHumans NMuscarinic acetylcholine receptor M4 antagonistHumans NMuscarinic acetylcholine receptor M5 antagonistHumans U5-hydroxytryptamine receptor 1A binderHumans U5-hydroxytryptamine receptor 2C binderHumans UDopamine D2 receptor binderHumans UAlpha-2 adrenergic receptors binderHumans - Absorption
Desipramine hydrochloride is rapidly and almost completely absorbed from the gastrointestinal tract. It undergoes extensive first-pass metabolism. Peak plasma concentrations are attained 4 - 6 hours following oral administration.
- Volume of distribution
Not Available
- Protein binding
73-92% bound to plasma proteins
- Metabolism
Desipramine is extensively metabolized in the liver by CYP2D6 (major) and CYP1A2 (minor) to 2-hydroxydesipramine, an active metabolite. 2-hydroxydesipramine is thought to retain some amine reuptake inhibition and may possess cardiac depressant activity. The 2-hydroxylation metabolic pathway of desipramine is under genetic control.
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- Route of elimination
Desipramine is metabolized in the liver, and approximately 70% is excreted in the urine.
- Half-life
7-60+ hours; 70% eliminated renally
- Clearance
Not Available
- Adverse Effects
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Male mice: LD50 = 290 mg/kg, female rats: LD50 = 320 mg/kg. Antagonism of the histamine H1 and α1 receptors can lead to sedation and hypotension. Antimuscarinic activity confers anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of desipramine. Cardiovascular side effects in postural hypotension, tachycardia, hypertension, ECG changes and congestive heart failure. Psychotoxic effects include impaired memory and delirium. Induction of hypomanic or manic episodes may occur in patients with a history of bipolar disorder. Withdrawal symptoms include GI disturbances (e.g. nausea, vomiting, abdominal pain, diarrhea), anxiety, insomnia, nervousness, headache and malaise.
- Pathways
Pathway Category Imipramine Action Pathway Drug action Desipramine Action Pathway Drug action Imipramine Metabolism Pathway Drug metabolism Desipramine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*4 (A;A) A Allele Effect Directly Studied Patients with this genotype have reduced metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*3 Not Available 2549delA Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*4 Not Available A allele Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for adverse side effects Details Cytochrome P450 2D6 CYP2D6*3 Not Available G allele Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details Cytochrome P450 2D6 CYP2D6*4 Not Available 3877G>A Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Desipramine is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Desipramine which could result in a higher serum level. Abatacept The metabolism of Desipramine can be increased when combined with Abatacept. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Desipramine. Abiraterone The metabolism of Desipramine can be decreased when combined with Abiraterone. - Food Interactions
- Avoid alcohol.
- Limit caffeine intake.
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Desipramine hydrochloride 1Y58DO4MY1 58-28-6 XAEWZDYWZHIUCT-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Pertofran (Ciba) / Pertofrane (USV)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desipramine Tablet 100 mg Oral Apotex Corporation 1996-09-13 Not applicable Canada 
Desipramine Tablet 10 mg Oral Apotex Corporation 1996-12-31 Not applicable Canada Desipramine Tablet 75 mg Oral Aa Pharma Inc 1996-12-31 Not applicable Canada Desipramine Tablet 10 mg Oral Aa Pharma Inc 1996-12-31 Not applicable Canada Desipramine Tablet 75 mg Oral Apotex Corporation 1996-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desipramine HCL Tablet 10 mg/1 Oral Direct_Rx 2022-11-16 Not applicable US 
Desipramine Hydrochloride Tablet, film coated 75 mg/1 Oral Actavis Pharma, Inc. 2006-05-08 Not applicable US Desipramine Hydrochloride Tablet, film coated 10 mg/1 Oral Alembic Pharmaceuticals Inc. 2021-07-08 Not applicable US Desipramine Hydrochloride Tablet, film coated 75 mg/1 Oral Sandoz Inc 1988-06-20 2024-02-29 US Desipramine Hydrochloride Tablet 50 mg/1 Oral Remedy Repack 2010-08-13 2011-08-13 US
Categories
- ATC Codes
- N06AA01 — Desipramine
- Drug Categories
- Adrenergic Agents
- Adrenergic Uptake Inhibitors
- Agents producing tachycardia
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Anticholinergic Agents
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Antidepressive Agents, Tricyclic
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dibenzazepines
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Histamine Antagonists
- Histamine H1 Antagonists
- Membrane Transport Modulators
- Muscarinic Antagonists
- Narrow Therapeutic Index Drugs
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Non-Selective Monoamine Reuptake Inhibitors
- OCT1 inhibitors
- OCT2 Inhibitors
- P-glycoprotein inhibitors
- Potential QTc-Prolonging Agents
- Psychoanaleptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Antagonists
- Tricyclics and Other Norepinephrine-reuptake Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Dibenzazepines
- Direct Parent
- Dibenzazepines
- Alternative Parents
- Alkyldiarylamines / Azepines / Benzenoids / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Dibenzazepine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- secondary amino compound, dibenzoazepine (CHEBI:47781)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- TG537D343B
- CAS number
- 50-47-5
- InChI Key
- HCYAFALTSJYZDH-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
- IUPAC Name
- (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine
- SMILES
- CNCCCN1C2=CC=CC=C2CCC2=CC=CC=C12
References
- Synthesis Reference
Biel, J.H.and Judd, C.I.; US. Patent 3,454,554; July 8,1969; assigned to Colgate Palmolive Co.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015282
- KEGG Drug
- D07791
- KEGG Compound
- C06943
- PubChem Compound
- 2995
- PubChem Substance
- 46504624
- ChemSpider
- 2888
- BindingDB
- 35229
- 3247
- ChEBI
- 47781
- ChEMBL
- CHEMBL72
- ZINC
- ZINC000001530611
- Therapeutic Targets Database
- DAP001151
- PharmGKB
- PA449233
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- DSM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Desipramine
- PDB Entries
- 2qb4 / 2qju / 7q19 / 7q2n / 7q2o / 7q2p
- FDA label
- Download (152 KB)
- MSDS
- Download (73.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Depression 1 4 Completed Treatment Major Depressive Disorder (MDD) 1 4 Completed Treatment Substance Related Disorders 1 4 Recruiting Health Services Research Chronic Pain 1 4 Terminated Treatment Neuroaxonal Dystrophy, Infantile 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Actavis Group
- Amerisource Health Services Corp.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Eon Labs
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Kaiser Foundation Hospital
- Major Pharmaceuticals
- Merrell Pharmaceuticals Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Nucare Pharmaceuticals Inc.
- Patheon Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prescription Dispensing Service Inc.
- Professional Co.
- Qualitest
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandhills Packaging Inc.
- Sandoz
- Sanofi-Aventis Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- UDL Laboratories
- United Research Laboratories Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral 50 mg Tablet Oral 150 mg Tablet Oral 10 mg/1 Tablet Oral 100 mg/1 Tablet Oral 150 mg/1 Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet Oral 75 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Tablet, sugar coated Oral 10 mg/1 Tablet, sugar coated Oral 100 mg/1 Tablet, sugar coated Oral 150 mg/1 Tablet, sugar coated Oral 25 mg/1 Tablet, sugar coated Oral 50 mg/1 Tablet, sugar coated Oral 75 mg/1 Tablet Oral 100 mg Tablet Oral 75 mg / tab Tablet Oral Tablet Oral 10 mg / tab Tablet Oral 25 mg / tab Tablet Oral 50 mg / tab Tablet Oral 10 mg Tablet Oral 25 mg Tablet Oral 75 mg - Prices
Unit description Cost Unit Desipramine hcl powder 14.4USD g Norpramin 150 mg tablet 6.08USD tablet Desipramine HCl 150 mg tablet 4.67USD tablet Norpramin 100 mg tablet 4.2USD tablet Norpramin 75 mg tablet 3.19USD tablet Desipramine HCl 100 mg tablet 2.81USD tablet Desipramine HCl 75 mg tablet 2.63USD tablet Norpramin 50 mg tablet 2.51USD tablet Desipramine 150 mg tablet 2.18USD tablet Desipramine HCl 50 mg tablet 1.64USD tablet Desipramine 100 mg tablet 1.5USD tablet Norpramin 25 mg tablet 1.33USD tablet Desipramine 75 mg tablet 1.15USD tablet Norpramin 10 mg tablet 1.11USD tablet Apo-Desipramine 75 mg Tablet 0.93USD tablet Desipramine 50 mg tablet 0.92USD tablet Desipramine HCl 10 mg tablet 0.87USD tablet Desipramine HCl 25 mg tablet 0.83USD tablet Apo-Desipramine 50 mg Tablet 0.7USD tablet Desipramine 25 mg tablet 0.49USD tablet Desipramine 10 mg tablet 0.4USD tablet Apo-Desipramine 10 mg Tablet 0.4USD tablet Apo-Desipramine 25 mg Tablet 0.4USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 214-218 °C Not Available water solubility 58.6 mg/L (at 24 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 4.90 HANSCH,C ET AL. (1995) logS -3.66 ADME Research, USCD Caco2 permeability -4.67 ADME Research, USCD pKa 10.4 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0396 mg/mL ALOGPS logP 4.02 ALOGPS logP 3.9 Chemaxon logS -3.8 ALOGPS pKa (Strongest Basic) 10.02 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 15.27 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 85.31 m3·mol-1 Chemaxon Polarizability 31.74 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9854 Caco-2 permeable + 0.8868 P-glycoprotein substrate Substrate 0.7945 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Non-inhibitor 0.6353 Renal organic cation transporter Inhibitor 0.7955 CYP450 2C9 substrate Non-substrate 0.7684 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.5117 CYP450 1A2 substrate Inhibitor 0.9029 CYP450 2C9 inhibitor Non-inhibitor 0.9125 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9241 CYP450 3A4 inhibitor Inhibitor 0.744 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8478 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9476 Biodegradation Not ready biodegradable 0.9686 Rat acute toxicity 2.8197 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8569 hERG inhibition (predictor II) Inhibitor 0.8604
Spectra
- Mass Spec (NIST)
- Download (11 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.9365098 predictedDarkChem Lite v0.1.0 [M-H]- 174.1489098 predictedDarkChem Lite v0.1.0 [M-H]- 156.60193 predictedDeepCCS 1.0 (2019) [M-H]- 174.9365098 predictedDarkChem Lite v0.1.0 [M-H]- 174.1489098 predictedDarkChem Lite v0.1.0 [M-H]- 156.60193 predictedDeepCCS 1.0 (2019) [M+H]+ 175.6632098 predictedDarkChem Lite v0.1.0 [M+H]+ 174.9812098 predictedDarkChem Lite v0.1.0 [M+H]+ 158.95993 predictedDeepCCS 1.0 (2019) [M+H]+ 175.6632098 predictedDarkChem Lite v0.1.0 [M+H]+ 174.9812098 predictedDarkChem Lite v0.1.0 [M+H]+ 158.95993 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.2829098 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.4296098 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.05309 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.2829098 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.4296098 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.05309 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Zavosh A, Schaefer J, Ferrel A, Figlewicz DP: Desipramine treatment decreases 3H-nisoxetine binding and norepinephrine transporter mRNA in SK-N-SHSY5Y cells. Brain Res Bull. 1999 Jul 1;49(4):291-5. [Article]
- Weinshenker D, White SS, Javors MA, Palmiter RD, Szot P: Regulation of norepinephrine transporter abundance by catecholamines and desipramine in vivo. Brain Res. 2002 Aug 16;946(2):239-46. [Article]
- Bryan-Lluka LJ, Bonisch H, Lewis RJ: chi-Conopeptide MrIA partially overlaps desipramine and cocaine binding sites on the human norepinephrine transporter. J Biol Chem. 2003 Oct 10;278(41):40324-9. Epub 2003 Jul 1. [Article]
- Zhu MY, Kyle PB, Hume AS, Ordway GA: The persistent membrane retention of desipramine causes lasting inhibition of norepinephrine transporter function. Neurochem Res. 2004 Feb;29(2):419-27. [Article]
- Ordway GA, Jia W, Li J, Zhu MY, Mandela P, Pan J: Norepinephrine transporter function and desipramine: residual drug effects versus short-term regulation. J Neurosci Methods. 2005 Apr 30;143(2):217-25. Epub 2004 Dec 30. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Holmes A, Yang RJ, Murphy DL, Crawley JN: Evaluation of antidepressant-related behavioral responses in mice lacking the serotonin transporter. Neuropsychopharmacology. 2002 Dec;27(6):914-23. [Article]
- Gould GG, Altamirano AV, Javors MA, Frazer A: A comparison of the chronic treatment effects of venlafaxine and other antidepressants on serotonin and norepinephrine transporters. Biol Psychiatry. 2006 Mar 1;59(5):408-14. Epub 2005 Sep 2. [Article]
- Zhou L, Huang KX, Kecojevic A, Welsh AM, Koliatsos VE: Evidence that serotonin reuptake modulators increase the density of serotonin innervation in the forebrain. J Neurochem. 2006 Jan;96(2):396-406. Epub 2005 Nov 21. [Article]
- Hoffman AF, Gerhardt GA: In vivo electrochemical studies of dopamine clearance in the rat substantia nigra: effects of locally applied uptake inhibitors and unilateral 6-hydroxydopamine lesions. J Neurochem. 1998 Jan;70(1):179-89. [Article]
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Matsumoto K, Ojima K, Ohta H, Watanabe H: Beta 2- but not beta 1-adrenoceptors are involved in desipramine enhancement of aggressive behavior in long-term isolated mice. Pharmacol Biochem Behav. 1994 Sep;49(1):13-8. [Article]
- Sapena R, Morin D, Zini R, Morin C, Tillement JP: Desipramine treatment differently down-regulates beta-adrenoceptors of freshly isolated neurons and astrocytes. Eur J Pharmacol. 1996 Apr 4;300(1-2):159-62. [Article]
- Abadie C, Foucart S, Page P, Nadeau R: Modulation of noradrenaline release from isolated human atrial appendages. J Auton Nerv Syst. 1996 Dec 14;61(3):269-76. [Article]
- Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [Article]
- Osadchii OE, Woodiwiss AJ, Deftereos D, Norton GR: Temporal changes in myocardial adrenergic regulation with the progression to pump dysfunction after chronic beta-adrenoreceptor activation in rats. Pflugers Arch. 2007 Nov;455(2):251-60. Epub 2007 Jun 9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- Sapena R, Morin D, Zini R, Morin C, Tillement JP: Desipramine treatment differently down-regulates beta-adrenoceptors of freshly isolated neurons and astrocytes. Eur J Pharmacol. 1996 Apr 4;300(1-2):159-62. [Article]
- Burgi S, Baltensperger K, Honegger UE: Antidepressant-induced switch of beta 1-adrenoceptor trafficking as a mechanism for drug action. J Biol Chem. 2003 Jan 10;278(2):1044-52. Epub 2002 Oct 21. [Article]
- Matsumoto K, Ojima K, Ohta H, Watanabe H: Beta 2- but not beta 1-adrenoceptors are involved in desipramine enhancement of aggressive behavior in long-term isolated mice. Pharmacol Biochem Behav. 1994 Sep;49(1):13-8. [Article]
- Samnick S, Scheuer C, Munks S, El-Gibaly AM, Menger MD, Kirsch CM: Technetium-99m labeled 1-(4-fluorobenzyl)-4-(2-mercapto-2-methyl-4-azapentyl)-4-(2-mercapto-2-methylprop ylamino)-piperidine and iodine-123 metaiodobenzylguanidine for studying cardiac adrenergic function: a comparison of the uptake characteristics in vascular smooth muscle cells and neonatal cardiac myocytes, and an investigation in rats. Nucl Med Biol. 2004 May;31(4):511-22. [Article]
- Mudunkotuwa NT, Horton RW: Desipramine administration in the olfactory bulbectomized rat: changes in brain beta-adrenoceptor and 5-HT2A binding sites and their relationship to behaviour. Br J Pharmacol. 1996 Apr;117(7):1481-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sphingomyelin phosphodiesterase activity
- Specific Function
- Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic ac...
- Gene Name
- SMPD1
- Uniprot ID
- P17405
- Uniprot Name
- Sphingomyelin phosphodiesterase
- Molecular Weight
- 69751.3 Da
References
- Testai FD, Landek MA, Dawson G: Regulation of sphingomyelinases in cells of the oligodendrocyte lineage. J Neurosci Res. 2004 Jan 1;75(1):66-74. [Article]
- Kolzer M, Werth N, Sandhoff K: Interactions of acid sphingomyelinase and lipid bilayers in the presence of the tricyclic antidepressant desipramine. FEBS Lett. 2004 Feb 13;559(1-3):96-8. [Article]
- Erdreich-Epstein A, Tran LB, Cox OT, Huang EY, Laug WE, Shimada H, Millard M: Endothelial apoptosis induced by inhibition of integrins alphavbeta3 and alphavbeta5 involves ceramide metabolic pathways. Blood. 2005 Jun 1;105(11):4353-61. Epub 2005 Feb 10. [Article]
- Zeidan YH, Pettus BJ, Elojeimy S, Taha T, Obeid LM, Kawamori T, Norris JS, Hannun YA: Acid ceramidase but not acid sphingomyelinase is required for tumor necrosis factor-{alpha}-induced PGE2 production. J Biol Chem. 2006 Aug 25;281(34):24695-703. Epub 2006 Jun 27. [Article]
- Hurwitz R, Ferlinz K, Sandhoff K: The tricyclic antidepressant desipramine causes proteolytic degradation of lysosomal sphingomyelinase in human fibroblasts. Biol Chem Hoppe Seyler. 1994 Jul;375(7):447-50. [Article]
- Kornhuber J, Tripal P, Reichel M, Muhle C, Rhein C, Muehlbacher M, Groemer TW, Gulbins E: Functional Inhibitors of Acid Sphingomyelinase (FIASMAs): a novel pharmacological group of drugs with broad clinical applications. Cell Physiol Biochem. 2010;26(1):9-20. doi: 10.1159/000315101. Epub 2010 May 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Sawynok J, Esser MJ, Reid AR: Peripheral antinociceptive actions of desipramine and fluoxetine in an inflammatory and neuropathic pain test in the rat. Pain. 1999 Aug;82(2):149-58. [Article]
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Components:
| Name | UniProt ID |
|---|---|
| Alpha-1A adrenergic receptor | P35348 |
| Alpha-1B adrenergic receptor | P35368 |
| Alpha-1D adrenergic receptor | P25100 |
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
- Palvimaki EP, Roth BL, Majasuo H, Laakso A, Kuoppamaki M, Syvalahti E, Hietala J: Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor. Psychopharmacology (Berl). 1996 Aug;126(3):234-40. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Components:
| Name | UniProt ID |
|---|---|
| Alpha-2A adrenergic receptor | P08913 |
| Alpha-2B adrenergic receptor | P18089 |
| Alpha-2C adrenergic receptor | P18825 |
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
- Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [Article]
- Isobe T, Hichiya H, Hanioka N, Yamamoto S, Shinoda S, Funae Y, Satoh T, Yamano S, Narimatsu S: Different effects of desipramine on bufuralol 1''-hydroxylation by rat and human CYP2D enzymes. Biol Pharm Bull. 2005 Apr;28(4):634-40. [Article]
- Yang TJ, Krausz KW, Sai Y, Gonzalez FJ, Gelboin HV: Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism. Drug Metab Dispos. 1999 Jan;27(1):102-9. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Ramey K, Ma JD, Best BM, Atayee RS, Morello CM: Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74. doi: 10.1093/jat/bku034. Epub 2014 Apr 29. [Article]
- Yang TJ, Krausz KW, Sai Y, Gonzalez FJ, Gelboin HV: Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism. Drug Metab Dispos. 1999 Jan;27(1):102-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Polasek TM, Miners JO: Time-dependent inhibition of human drug metabolizing cytochromes P450 by tricyclic antidepressants. Br J Clin Pharmacol. 2008 Jan;65(1):87-97. doi: 10.1111/j.1365-2125.2007.02964.x. Epub 2007 Jul 27. [Article]
- Ramey K, Ma JD, Best BM, Atayee RS, Morello CM: Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74. doi: 10.1093/jat/bku034. Epub 2014 Apr 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. doi: 10.1002/jps.2600750208. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]
- Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [Article]
- Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [Article]
- Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [Article]
- Duan H, Hu T, Foti RS, Pan Y, Swaan PW, Wang J: Potent and Selective Inhibition of Plasma Membrane Monoamine Transporter by HIV Protease Inhibitors. Drug Metab Dispos. 2015 Nov;43(11):1773-80. doi: 10.1124/dmd.115.064824. Epub 2015 Aug 18. [Article]
- Han TK, Everett RS, Proctor WR, Ng CM, Costales CL, Brouwer KL, Thakker DR: Organic cation transporter 1 (OCT1/mOct1) is localized in the apical membrane of Caco-2 cell monolayers and enterocytes. Mol Pharmacol. 2013 Aug;84(2):182-9. doi: 10.1124/mol.112.084517. Epub 2013 May 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Toxin transporter activity
- Specific Function
- Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
- Gene Name
- SLC22A3
- Uniprot ID
- O75751
- Uniprot Name
- Solute carrier family 22 member 3
- Molecular Weight
- 61279.485 Da
References
- Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [Article]
- Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [Article]
- Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [Article]
- Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55